Great ideas! Go ahead with the PR @vitor as I'm traveling this week and won't have time to put some of these ideas into action.
A useful flag for howdoi will be -j for JSON output to populate the text field. You could also pass -n3 to get up to three potential answers.
The last time I checked, homebrew was reluctant to add utilities that could already be installed via pip. I agree that the way this plugin is configured now is annoying.